6-isopropyl-9-(tetrahydro-2H-pyran-2-yl)purine | 175787-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-isopropyl-9-(tetrahydro-2H-pyran-2-yl)purine
• 英文别名: 9-(Oxan-2-yl)-6-propan-2-ylpurine
• CAS: 175787-71-0
• 化学式: C₁₃H₁₈N₄O
• 分子量: 246.312
• InChiKey: BJZRPYUTWCGARK-UHFFFAOYSA-N

物化性质

• 沸点：
  412.8±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-isopropyl-9-(tetrahydro-2H-pyran-2-yl)purine 在 硫酸 、 水 作用下， 反应 24.0h， 以75%的产率得到6-Isopropylpurine
  参考文献：
  名称：

  Synthesis of Acyclic Nucleotide Analogues Derived from 6-(sec- or tert-Alkyl)purines via Coupling of 6-Chloropurine Derivatives with Organocuprates

  摘要：

  将9-[2-(二异丙氧基磷酰甲氧基)乙基]-6-氯嘌呤（23）（和（R）-9-[2-(二异丙氧基磷酰甲氧基)丙基]-6-氯嘌呤（24）分别）与由格氏试剂衍生的有机铜盐偶联，在去保护后得到6-(sec-或tert-烷基)磷酸酯31-36。作为模型，还制备了一系列6-(sec-或tert-烷基)嘌呤2-12。

  DOI：

  10.1135/cccc19982065
• 作为产物：
  描述：

  异丙基溴化镁 、 6-氯-9-(四氢-2-吡喃基)嘌呤 在 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以67%的产率得到6-isopropyl-9-(tetrahydro-2H-pyran-2-yl)purine
  参考文献：
  名称：

  6-氯嘌呤与格氏试剂衍生的有机铜的偶合：仲和叔6-烷基嘌呤的便捷途径

  摘要：

  可以通过在非常温和的条件下通过CuI介导的第二或第三级格氏试剂与9-取代的6-氯嘌呤的CuI介导的反应，方便地制备在6位上带有仲或叔烷基的嘌呤衍生物。

  DOI：

  10.1016/0040-4039(95)02375-5

文献信息

• Nicotinamide Derivatives
  申请人：Blake Tanisha D.

  公开号：US20080146569A1

  公开（公告）日：2008-06-19

  The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are as defined herein, compositions containing such compounds and the uses of such compounds for the treatment of various diseases and conditions such as asthma.

  本发明涉及公式（I）的化合物及其药用可接受的盐和溶剂化合物，其中取代基如本文所定义，包含这种化合物的组合物以及这种化合物用于治疗各种疾病和状况，如哮喘。
• Heterocyclic compounds useful in treating diseases and conditions
  申请人：Blake Tanisha D.

  公开号：US20080207651A1

  公开（公告）日：2008-08-28

  The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are as defined herein, compositions containing such compounds and the uses of such compounds for the treatment of various diseases and conditions such as asthma.

  本发明涉及公式（I）化合物及其药学上可接受的盐和溶剂化物，其中取代基如本文所定义，包含此类化合物的组合物以及此类化合物用于治疗各种疾病和病况，如哮喘的用途。
• Heterocyclic Compounds Useful in Treating Diseases and Conditions
  申请人：Blake Tanisha D.

  公开号：US20090281125A1

  公开（公告）日：2009-11-12

  The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts and solvates thereof, wherein the substituents are as defined herein, compositions containing such compounds and the uses of such compounds for the treatment of various diseases and conditions such as asthma.

  本发明涉及公式（I）的化合物及其药学上可接受的盐和溶剂化物，其中取代基的定义如本文所述，包含这种化合物的组合物以及利用这种化合物治疗哮喘等各种疾病和病况的用途。
• Regioselective Metalation of 6-Methylpurines: Synthesis of Fluoromethyl Purines and Related Nucleosides for Suicide Gene Therapy of Cancer
  作者：Abdalla E. A. Hassan、William B. Parker、Paula W. Allan、John A. Secrist

  DOI：10.1080/15257770903091938

  日期：2009.8.11

  Metalation of 6-methyl-9-(tetrahydro-2H-pyran-2-yl)purine (10) with lithiating agents of varying basicities such as n-BuLi and LiHMDS in THF at - 78 degrees C resulted in metalation at both of the 6-CH3 moiety and the 8-CH position, irrespective of the molar equivalence of the base. On the other hand, a regioselective metalation at the 6-CH3 moiety of 10 was observed with NaHMDS or KHMDS, under similar conditions. Treatment of the potassium salts of 10 and of the protected riboside derivative 6-methyl-9-(beta-D-2,3,5-tri-O-tert-butyldimethylsilylribofuranosyl)purine (22) with N-fluorobenzenesulfonamide (NFSI) at - 78 degrees C gave the corresponding 6-fluoromethylpurine derivatives 11 and 23, respectively, in good yields. Deprotection of 11 and 23 under standard conditions gave 6-fluoromethylpurine (6-FMeP, 3) and 6-fluoromethyl-9-(beta-D-ribofuranosyl)purine (6-FMePR, 4), respectively, in high yield. Both 3 and 4 demonstrated cytotoxic activity against CCRF-CEM cells in culture. 6-FMePR is a good substrate for E. coli purine nucleoside phosphorylase (E. coli PNP) with a comparable substrate activity to that of the parent nucleoside, 6-methyl-9-(beta-D-ribofuranosyl)purine (&MePA 21). The cytotoxic activity of 6-FMeP along with the substrate activity of 6-FMePR with E. coli PNP meet the fundamental requirements for using 6-FMeP as a Potential toxin in PAT/prodrug based cancer gene therapy.
• Selective Metalation of 6-Methylpurines: Synthesis of 6-Fluoromethylpurines and Related Nucleosides
  作者：Abdalla E. A. Hassan、William B. Parker、Paula W. Allan、John A. Montgomery、John A. Secrist

  DOI：10.1081/ncn-120022625

  日期：2003.10

  A selective metalation at the 6-CH3 over C-8 of 6-methylpurine derivative 6 was observed with softer counter cation (Na+ or K+) of the base, while the harder Li+ showed no selectivity. In the presence of N-fluorobenzenesulfonamide (NFSI), this property was utilized for the synthesis of 6-fluoromethylpurine derivatives 4 and 5 as potential toxins for suicide gene therapy.